Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

ABSTRACT

An organometallic compound represented by Formula 1: 
       M 1 (Ln 1 ) n1 (L n2 ) 3-n1   Formula 1
 
     wherein M 1  is a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements, Ln 1  is a bidentate ligand, n1 is 0, 1, or 2, and Ln 2  is a ligand represented by Formula 1A: 
     
       
         
         
             
             
         
       
         
         
           
             wherein A 1 , A 2 , Y 1 , Y 2 , R 1  to R 3 , R 10 , R 20 , b10, and b20 are as provided herein, and 
             * and *′ each indicate a binding site to a neighboring atom.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2020-0122432, filed on Sep. 22, 2020, in the KoreanIntellectual Property Office, and all the benefits accruing therefromunder 35 U.S.C. § 119, the content of which is incorporated by referenceherein in its entirety.

BACKGROUND 1. Field

One or more embodiments of the present disclosure relates toorganometallic compounds, organic light-emitting devices including thesame, and electronic apparatuses including the organic light-emittingdevices.

2. Description of Related Art

Organic light-emitting devices are self-emission devices, which haveimproved characteristics in terms of viewing angles, response time,brightness, driving voltage, and response speed, and produce full-colorimages.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer between the anode and the cathode, whereinthe organic layer includes an emission layer. A hole transport regionmay be arranged between the anode and the emission layer, and anelectron transport region may be arranged between the emission layer andthe cathode. Holes provided from the anode may move toward the emissionlayer through the hole transport region, and electrons provided from thecathode may move toward the emission layer through the electrontransport region. The holes and the electrons recombine in the emissionlayer to produce excitons. These excitons transition from an excitedstate to a ground state to thereby generate visible light.

SUMMARY

Provided are organometallic compounds, organic light-emitting devicesincluding the same, and electronic apparatuses including the organiclight-emitting devices.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments of the disclosure.

According to an aspect of one or more embodiments, provided is anorganometallic compound represented by Formula 1:

wherein, in Formula 1,

M₁ is a first-row transition metal of the Periodic Table of Elements, asecond-row transition metal of the Periodic Table of Elements, or athird-row transition metal of the Periodic Table of Elements,

Ln₁ is a bidentate ligand,

n1 is 0, 1, or 2, and

Ln₂ is a ligand represented by Formula 1A, and

in Formulae 1A and 1-1,

A₁, A₃, and A₄ are each independently a C₅-C₃₀ carbocyclic group or aC₁-C₃₀ heterocyclic group,

A₂ is (i) a 6-membered carbocyclic group or a 6-membered heterocyclicgroup or (ii) a bi- or multi-cyclic C₅-C₃₀ carbocyclic group includingat least one of a 6-membered carbocyclic group and a 6-memberedheterocyclic group or a bi- or multi-cyclic C₁-C₃₀ heterocyclic groupincluding at least one of a 6-membered carbocyclic group and a6-membered heterocyclic group,

Y₁ is C or N, and Y₂ is C or N,

R₁, R₂, and R₃ are each independently a group represented by Formula1-1, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), —B(Q₁)(Q₂),—P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂),

at least one of R₁, R₂, and R₃ is a group represented by Formula 1-1,

R₁₀, R₂₀, R₃₀, and R₄₀ are each independently hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted a C₁-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₁-C₆₀ heteroarylthio group, a substituted orunsubstituted C₂-C₆₀ heteroarylalkyl group, a substituted orunsubstituted C₂-C₆₀ alkylheteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂),—P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂),

at least two neighboring groups among R₁₀, R₂₀, R₃₀, and R₄₀ areoptionally linked together to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup,

b10 and b20 are each independently an integer from 1 to 10,

b30 and b40 are each independently an integer from 1 to 10,

when A₁ is a benzene group, (i) at least one of R₂₀(s) in the number ofb20 is a substituted or unsubstituted C₁-C₆₀ alkyl group,—Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃), or (ii) R₁ or R₂ is a grouprepresented by Formula 1-1,

* and *′ each indicate a binding site to a neighboring atom, and

at least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₇-C₆₀arylalkyl group, the substituted C₁-C₆₀ heteroaryl group, thesubstituted C₁-C₆₀ heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio group, the substituted C₂-C₆₀ heteroarylalkyl group, thesubstituted C₂-C₆₀ alkylheteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group is:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, or a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each substituted with one or more of deuterium,—F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —Ge(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₆)(Q₁₇),—P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, aC₂-C₆₀ alkylheteroaryl group, a monovalent non-aromatic condensedpolycyclic group, or a monovalent non-aromatic condensedheteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,or a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with one or more of deuterium, —F, —Cl, —Br, —I, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, aC₂-C₆₀ alkylheteroaryl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —Ge(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₆)(Q₂₇)-P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —Ge(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are eachindependently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to an aspect of another embodiment, there is provided anorganic light-emitting device including: a first electrode; a secondelectrode; and an organic layer arranged between the first electrode andthe second electrode and including an emission layer, wherein theorganic layer includes at least one organometallic compound as providedherein.

The organometallic compound as provided herein may be included in theemission layer of the organic layer, and the organometallic compoundincluded in the emission layer may act as a dopant.

According to an aspect of another embodiment, there is provided anelectronic apparatus including the organic light-emitting device asdescribed herein.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, features, and advantages of certainembodiments of the disclosure will be more apparent from the followingdescription taken in conjunction with the FIGURE, which shows aschematic cross-sectional view of an organic light-emitting deviceaccording to one or more embodiments.

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examplesof which are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present exemplary embodiments may have different forms and shouldnot be construed as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the figures, in further detail to explain aspects. As usedherein, the term “and/or” includes any and all combinations of one ormore of the associated listed items. Expressions such as “at least oneof,” when preceding a list of elements, modify the entire list ofelements and do not modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to a crosssection illustration that is a schematic illustration of one or moreidealized embodiments. As such, variations from the shapes of theillustration as a result, for example, of manufacturing techniquesand/or tolerances, are to be expected. Thus, embodiments describedherein should not be construed as limited to the particular shapes ofregions as illustrated herein but are to include deviations in shapesthat result, for example, from manufacturing. For example, a regionillustrated or described as flat may, typically, have rough and/ornonlinear features. Moreover, sharp angles that are illustrated may berounded. Thus, the regions illustrated in the FIGURE are schematic innature and their shapes are not intended to illustrate the precise shapeof a region and are not intended to limit the scope of the presentclaims.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within +30%, 20%, 10%, 5% of the stated value.

An aspect of the present disclosure provides an organometallic compoundrepresented by Formula 1:

M₁(Ln₁)_(n1)(Ln₂)_(3-n1)  Formula 1

wherein, M₁ in Formula 1 is a first-row transition metal of the PeriodicTable of Elements, a second-row transition metal of the Periodic Tableof Elements, or a third-row transition metal of the Periodic Table ofElements.

In one or more embodiments, M₁ may be beryllium (Be), magnesium (Mg),aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co),copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr),ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re),iridium (Ir,), osmium (Os), platinum (Pt), or gold (Au).

In one or more embodiments, M₁ may be Ir, Os, Pt, Pd, or Au.

In one or more embodiments, M₁ may be Ir.

In Formula 1, Ln₁ may be a bidentate ligand.

In Formula 1, n1 may be 0, 1, or 2.

In Formula 1, Ln₂ may be a ligand represented by Formula 1A:

In Formulae 1A and 1-1, A₁, A₃, and A₄ may each independently be aC₅-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclic group.

For example, A₁, A₃, and A₄ may each independently be i) a first ring,ii) a second ring, iii) a condensed ring in which two or more firstrings are condensed with each other, iv) a condensed ring in which twoor more second rings are condensed with each other, or v) a condensedring in which one or more first rings and one or more second rings arecondensed with each other,

wherein the first ring may be a cyclopentane group, a cyclopentadienegroup, a furan group, a thiophene group, a pyrrole group, a silolegroup, an indene group, a benzofuran group, a benzothiophene group, anindole group, a benzosilole group, an oxazole group, an isoxazole group,an oxadiazole group, an isozadiazole group, an oxatriazole group, anisoxatriazole group, a thiazole group, an isothiazole group, athiadiazole group, an isothiadiazole group, a thiatriazole group, anisothiatriazole group, a pyrazole group, an imidazole group, a triazolegroup, a tetrazole group, an azasilole group, a diazasilole group, or atriazasilole group, and

the second ring may be an adamantane group, a norbornene group, abicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, abicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, acyclohexane group, a cyclohexene group, a benzene group, a pyridinegroup, a pyrimidine group, a pyrazine group, a pyridazine group, or atriazine group.

In one or more embodiments, A₁ to A₄ may each independently be a benzenegroup, a naphthalene group, an anthracene group, a phenanthrene group, atriphenylene group, a pyrene group, a chrysene group, a1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, apyrrole group, a cyclopentadiene group, a silole group, a borole group,a phosphole group, a selenophene group, a germole group, abenzothiophene group, a benzofuran group, an indole group, an indenegroup, a benzosilole group, a benzoborole group, a benzophosphole group,a benzoselenophene group, a benzogermole group, a dibenzothiophenegroup, a dibenzofuran group, a carbazole group, a fluorene group, adibenzosilole group, a dibenzoborole group, a dibenzophosphole group, adibenzoselenophene group, a dibenzogermole group, a dibenzothiophene5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxidegroup, an azabenzothiophene group, an azabenzofuran group, an azaindolegroup, an azaindene group, an azabenzosilole group, an azabenzoborolegroup, an azabenzophosphole group, an azabenzoselenophene group, anazabenzogermole group, an azadibenzothiophene group, an azadibenzofurangroup, an azacarbazole group, an azafluorene group, an azadibenzosilolegroup, an azadibenzoborole group, an azadibenzophosphole group, anazadibenzoselenophene group, an azadibenzogermole group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrazole group, animidazole group, a triazole group, an oxazole group, an isoxazole group,a thiazole group, isothiazole group, an oxadiazole group, a thiadiazolegroup, a benzopyrazole group, a benzimidazole group, a benzoxazolegroup, a benzothiazole group, a benzoxadizole group, a benzothiadiazolegroup, a 5,6,7,8-tetrahydroisoquinoline group, a5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornanegroup, or a norbornene group.

In one or more embodiments, A₁ may be a benzene group, a naphthalenegroup, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, abenzofuran group, an indole group, an indene group, a benzosilole group,a dibenzothiophene group, a dibenzofuran group, a carbazole group, afluorene group, or a dibenzosilole group.

In one or more embodiments, A₁ may be a benzene group, adibenzothiophene group, a dibenzofuran group, a carbazole group, afluorene group, or a dibenzosilole group.

In Formula 1A, A₂ may be (i) a 6-membered carbocyclic group or a6-membered heterocyclic group or (ii) a bi- or multi-cyclic C₅-C₃₀carbocyclic group including at least one of a 6-membered carbocyclicgroup and a 6-membered heterocyclic group or a bi- or multi-cyclicC₁-C₃₀ heterocyclic group including at least one of a 6-memberedcarbocyclic group and a 6-membered heterocyclic group.

In one or more embodiments, A₂ may be an azabenzothiophene group, anazabenzofuran group, an azaindole group, an azaindene group, anazabenzosilole group, an azabenzoborole group, an azabenzophospholegroup, an azabenzoselenophene group, an azabenzogermole group, anazadibenzothiophene group, an azadibenzofuran group, an azacarbazolegroup, an azafluorene group, an azadibenzosilole group, anazadibenzoborole group, an azadibenzophosphole group, anazadibenzoselenophene group, an azadibenzogermole group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinolinegroup.

In one or more embodiments, A₂ may be a pyridine group, a pyrimidinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a quinoxaline group, a quinazoline group, or aphenanthroline group.

In one or more embodiments, A₃ and A₄ may each independently be abenzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalenegroup, a benzothiophene group, a benzofuran group, an indole group, anindene group, a benzosilole group, a dibenzothiophene group, adibenzofuran group, a carbazole group, a fluorene group, or adibenzosilole group.

In one or more embodiments, A₃ and A₄ may each independently be abenzene group, a dibenzothiophene group, a dibenzofuran group, acarbazole group, a fluorene group, or a dibenzosilole group.

In Formula 1A, Y₁ may be C or N, and Y₂ may be C or N.

In Formulae 1 and 1A, a bond between M₁ and Y₁ may be a covalent bond ora coordinate bond.

In Formulae 1 and 1A, a bond between M₁ and Y₂ may be a covalent bond ora coordinate bond.

In one or more embodiments, Y₁ may be C, Y₂ may be N, a bond between M₁and Y₁ may be a covalent bond, and a bond between M₁ and Y₂ may be acoordinate bond.

In Formula 1A, R₁, R₂, and R₃ may each independently be a grouprepresented by Formula 1-1, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), —B(Q₆)(Q₇),—P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂), and

at least one of R₁, R₂, and R₃ may be a group represented by Formula1-1.

In one or more embodiments, R₁, R₂, and R₃ may each independently be:

a group represented by Formula 1-1;

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, —SF₅, a C₁-C₂₀alkyl group C₂-C₂₀ alkenyl group, a C₁-C₂₀ alkoxy group, or a C₁-C₂₀alkylthio group;

a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₂₀ alkoxy group, ora C₁-C₂₀ alkylthio group, each substituted with one or more ofdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group,a cycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group (a bicyclo[2.2.1]heptyl group), a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.2]octyl group, a (C₁-C₂₀ alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀ alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀ alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀ alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀ alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀ alkyl)bicyclo[1.1.1]pentyl group, a(C₁-C₂₀ alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀ alkyl)phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, or a pyrimidinyl group,

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexylgroup, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranylgroup, or azadibenzothiophenyl group, each unsubstituted or substitutedwith one or more of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a deuteratedC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.2]octyl group, a (C₁-C₂₀ alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀ alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀ alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀ alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀ alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀ alkyl)bicyclo[1.1.1]pentyl group, a(C₁-C₂₀ alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀ alkyl)phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranylgroup, or an azadibenzothiophenyl group; or

—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), —B(Q₁)(Q₂),—P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂),

wherein Q₁ to Q₅ may each independently be:

deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H,—CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H,—CD₂CDH₂, —CF₃, —CF₂H, —CFH₂, —CH₂CF₃, —CH₂CF₂H, —CH₂CFH₂, —CHFCH₃,—CHFCF₂H, —CHFCFH₂, —CHFCF₃, —CF₂CF₃, —CF₂CF₂H, or —CF₂CFH₂; or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an n-pentyl group, atert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentylgroup, a 3-pentyl group, a sec-isopentyl group, a phenyl group, abiphenyl group, or a naphthyl group, each unsubstituted or substitutedwith deuterium, —F, C₁-C₁₀ alkyl group, or a phenyl group, and

at least one of R₁, R₂, and R₃ may be a group represented by Formula1-1.

In one or more embodiments, R₁, R₂, and R₃ may each independently be agroup represented by Formula 1-1, hydrogen, deuterium, a methyl group,an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, atert-pentyl group, a neo-pentyl group, a 3-pentyl group, a3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C₁-C₂₀alkylphenyl group, a naphthyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃),

wherein at least one of R₁, R₂, and R₃ may be a group represented byFormula 1-1.

In one or more embodiments, any one of R₁ to R₃ may be a grouprepresented by Formula 1-1.

For example, R₂ may be a group represented by Formula 1-1, and each ofR₁ and R₃ may be hydrogen.

In Formulae 1A and 1-1, R₁₀, R₂₀, R₃₀, and R₄₀ may each independently behydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂).

In Formulae 1A and 1-1, R₁₀, R₂₀, R₃₀, and R₄₀ may each independentlybe:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, —SF₅, a C₁-C₂₀alkyl group C₂-C₂₀ alkenyl group, a C₁-C₂₀ alkoxy group, or a C₁-C₂₀alkylthio group;

a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₂₀ alkoxy group, ora C₁-C₂₀ alkylthio group, each substituted with one or more ofdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group,a cycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group (a bicyclo[2.2.1]heptyl group), a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.2]octyl group, a (C₁-C₂₀ alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀ alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀ alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀ alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀ alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀ alkyl)bicyclo[1.1.1]pentyl group, a(C₁-C₂₀ alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀ alkyl)phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, or a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexylgroup, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranylgroup, or azadibenzothiophenyl group, each unsubstituted or substitutedwith one or more of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a deuteratedC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.2]octyl group, a (C₁-C₂₀ alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀ alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀ alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀ alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀ alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀ alkyl)bicyclo[1.1.1]pentyl group, a(C₁-C₂₀ alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀ alkyl)phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranylgroup, or an azadibenzothiophenyl group; or

—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), or —B(Q₁)(Q₂),

wherein Q₁ to Q₅ may each independently be:

deuterium, —F, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H,—CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H,—CD₂CDH₂, —CF₃, —CF₂H, —CFH₂, —CH₂CF₃, —CH₂CF₂H, —CH₂CFH₂, —CHFCH₃,—CHFCF₂H, —CHFCFH₂, —CHFCF₃, —CF₂CF₃, —CF₂CF₂H, or —CF₂CFH₂; or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an n-pentyl group, atert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentylgroup, a 3-pentyl group, a sec-isopentyl group, a phenyl group, abiphenyl group, or a naphthyl group, each unsubstituted or substitutedwith deuterium, —F, C₁-C₁₀ alkyl group, or a phenyl group.

In Formula 1A, b10 indicates the number of R₁₀(s), and may be an integerfrom 1 to 10. In Formula 1A, b20 indicates the number of R₂₀(s), and maybe an integer from 1 to 10.

In Formula 1-1, b30 indicates the number of R₃₀(s), and may be aninteger from 1 to 10. In Formula 1-1, b40 indicates the number ofR₄₀(s), and may be an integer from 1 to 10.

In one or more embodiments, R₁₀, R₂₀, R₃₀, and R₄₀ may eachindependently be a group represented by one of Formulae 9-1 to 9-43,9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350:

wherein, in Formulae 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and10-201 to 10-350, * indicates a binding site to a neighboring atom, Phis phenyl group, TMS is a trimethylsilyl group, and TMG is atrimethylgermyl group.

In Formula 1A, when A₁ is a benzene group, (i) at least one of R₂₀(s) inthe number of b20 may be a substituted or unsubstituted C₁-C₆₀ alkylgroup, —Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃), or (ii) R₁ or R₂ may be agroup represented by Formula 1-1.

In Formula 1-1, * indicates a binding site to a neighboring atom inFormula 1.

In one or more embodiments, R₂₀ may be hydrogen, deuterium, a methylgroup, an ethyl group, an n-propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, ann-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentylgroup, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C₁-C₂₀alkylphenyl group, a naphthyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃).

In Formula 1A, * and *′ each indicate a binding site to a neighboringatom.

In Formulae 1A and 1-1, at least two neighboring groups among R₁₀, R₂₀,R₃₀, and R₄₀ may optionally be linked together form a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₁-C₃₀ heterocyclic group.

In one or more embodiments, at least two neighboring groups among R₁₀,R₂₀, R₃₀, and R₄₀ may optionally be linked together via a single bond, adouble bond, or a first linking group, to form a C₅-C₃₀ carbocyclicgroup that is unsubstituted or substituted with at least one R_(10a) ora C₁-C₃₀ heterocyclic group that is unsubstituted or substituted with atleast one R_(10a) (for example, a fluorene group, a xanthene group, anacridine group, or the like, each unsubstituted or substituted with atleast one R_(10a)), wherein R_(10a) may be the same as described inconnection with R₁₀.

The first linking group may be *—N(R₈)—*′, *—B(R₈)—*′, *—P(R₈)—*′,*—C(R₈)(R₉)—*, *—Si(R₈)(R₉)—*′, *—Ge(R₈)(R₉)—*′, *—S—*′, *—Se—*′,*—O—*′, *—C(═O)—*′ *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₈)=*′, *═C(R₈)—*′,*—C(R₈)═C(R₉)—*′, *—C(═S)—*′, or *—C═C*′, wherein R₈ and R₉ may each bethe same as described in connection with R₁₀, and * and *′ each indicatea binding site to a neighboring atom.

In one or more embodiments, Ln₁ may be represented by one of Formulae8-1 to 8-12, or in one or more embodiments, Ln₂ may be represented byFormula 5:

wherein, in Formula 5,

A₅ and A₆ may each independently be a C₅-C₃₀ carbocyclic group or aC₁-C₃₀ heterocyclic group,

Y₅ may be C or N, and Y₆ may be C or N,

R₅₀ and R₆₀ may each independently be hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂),

b50 and b60 may each independently be an integer from 1 to 10, and

* and *′ each indicate a binding site to a neighboring atom.

In one or more embodiments, A₅ may be a pyridine group, a pyrimidinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a quinoxaline group, a quinazoline group, aphenanthroline group, a pyrazole group, a triazole group, an imidazolegroup, an indole group, a benzopyrazole group, or a benzimidazole group.

In one or more embodiments, A₆ may be a benzene group, a naphthalenegroup, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, abenzofuran group, an indole group, an indene group, a benzosilole group,a dibenzothiophene group, a dibenzofuran group, a carbazole group, afluorene group, or a dibenzosilole group.

In one or more embodiments, Y₅ may be N, and Y₆ may be C,

a bond between M₁ and Y₅ may be a coordinate bond, and

a bond between M₁ and Y₆ may be a covalent bond.

In one or more embodiments, R₅₀ and R₆₀ may each independently be thesame as described in connection with R₁₀, R₂₀, R₃₀, or R₄₀.

In one or more embodiments, Ln₁ may be one of Formulae 5-1 to 5-116:

wherein, in Formulae 5-1 to 5-116,

R₅₁ to R₅₃ may each independently be hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, —SF₅, a C₁-C₂₀ alkyl group, ora C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group, each substituted with oneor more of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, a bicyclo[2.2.1]heptanyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a C₁-C₂₀ alkylphenyl group, a naphthyl group, a pyridinyl group,or a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, a bicyclo[2.2.1]heptanyl group, an adamantanyl group,a norbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a C₁-C₂₀ alkylphenyl group, a naphthyl group, a fluorenyl group,a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, or animidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, a bicyclo[2.2.1]heptanyl group, an adamantanyl group,a norbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a C₁-C₂₀ alkylphenyl group, a naphthyl group, a fluorenyl group,a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, or animidazopyrimidinyl group, each substituted with one or more ofdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, a bicyclo[2.2.1]heptanyl group, an adamantanyl group,a norbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a C₁-C₂₀ alkylphenyl group, a naphthyl group, a fluorenyl group,a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —B(Q₁₁)(Q₁₂), or—N(Q₁₁)(Q₁₂); or

—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), or —N(Q₁)(Q₂),

wherein Q₁ to Q₃ and Q₁₁ to Q₁₃ may each independently be:

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, asec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentylgroup, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, aC₁-C₂₀ alkylphenyl group, or a naphthyl group; and

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, asec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentylgroup, a 3-methyl-2-butyl group, a phenyl group, or a naphthyl group,each substituted with one or more of deuterium or a phenyl group.

In Formulae 5-1 to 5-116, b51 and b54 may each independently be 1 or 2;

b53 and b55 may each independently be 1, 2, or 3;

b52 may be 1,2,3, or 4;

Ph may be a phenyl group;

Ph-d5 may be a phenyl group in which each hydrogen is substituted withdeuterium; and

* and *′ each indicate a binding site to a neighboring atom.

In one or more embodiments, the organometallic compound may be acompound represented by one of Formulae 11-1 to 11-3:

wherein, in Formulae 11-1 to 11-3,

M₁, n1, A₂, R₁, R₂, R₃, R₁₀, R₂₀, and b20 may each be same as describedherein,

A₁₁ may be a benzene group, an indene group, an indole group, abenzofuran group, a benzothiophene group, or a benzosilole group,

b11 may be 1, 2, 3, 4, 5, or 6, R₁₁ and R₁₂ may each independently bethe same as described in connection with R₁₀,

A₅ and A₆ may each independently be a C₅-C₃₀ carbocyclic group or aC₁-C₃₀ heterocyclic group,

R₅₀ and R₆₀ may each independently be hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂), and

b50 and b60 may each independently be an integer from 1 to 10.

In one or more embodiments, in Formulae 11-1 and 11-2, (i) at least oneof R₂₀(s) in the number of b20 may be a substituted or unsubstitutedC₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃), or (ii) R₁ orR₂ may be a group represented by Formula 1-1.

In one or more embodiments, the organometallic compound may berepresented by Formula 12-1:

wherein, in Formula 12-1,

M₁, n1, A₁, R₁, R₂, R₃, R₁₀, and b10 may each be same as describedherein,

R₂₁ to R₂₄ may each independently be the same as described in connectionwith R₂₀,

A₅ and A₆ may each independently be a C₅-C₃₀ carbocyclic group or aC₁-C₃₀ heterocyclic group,

R₅₀ and R₆₀ may each independently be hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂), and

b50 and b60 may each independently be an integer from 1 to 10.

In one or more embodiments, in Formula 12-1, when A₁ is a benzene group,(i) at least one of R₂₁ to R₂₄ may be a substituted or unsubstitutedC₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃), or (ii) R₁ orR₂ may be a group represented by Formula 1-1.

In one or more embodiments, in Formula 12-1, when A₁ is a benzene group,(i) at least one of R₂₂ and R₂₃ may be a substituted or unsubstitutedC₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃), or (ii) R₁ orR₂ may be a group represented by Formula 1-1.

In one or more embodiments, the organometallic compound may berepresented by one of Formulae 21-1 to 21-5:

wherein, in Formulae 21-1 to 21-5,

M₁, n1, R₁, and R₂ may each be the same as described herein,

X₁ may be O, S, N(R₁₅), C(R₁₅)(R₁₆), or Si(R₁₅)(R₁₆),

R₁₁ to R₁₆ may each independently be the same as described in connectionwith R₁₀,

R₂₁ to R₂₄ may each independently be the same as described in connectionwith R₂₀,

R₅₁ to R₅₄ may each independently be the same as described in connectionwith R₅₀, and

R₆₁ to R₆₄ may each independently be the same as described in connectionwith R₆₀.

In one or more embodiments, in Formulae 21-1 and 21-2, (i) at least oneof R₂₁ to R₂₄ (or at least one of R₂₂ and R₂₃) may be a substituted orunsubstituted C₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or —Ge(Q₁)(Q₂)(Q₃),or (ii) R₁ or R₂ may be a group represented by Formula 1-1.

In one or more embodiments, in Formulae 21-3 to 21-5, R₁ or R₂ may be agroup represented by Formula 1-1.

In one or more embodiments, each ligand Ln₂ in Formula 1 may beindependently represented by one of Formulae 2-1 to 2-27:

wherein, in Formulae 2-1 to 2-27,

X₁ may be O, S, N(R₁₅), C(R₁₅)(R₁₆), or Si(R₁₅)(R₁₆),

R₁₅ and R₁₆ may each independently be the same as described inconnection with R₁₀,

R₂₂ and R₂₃ may each independently be a C₁-C₂₀ alkyl group,—Si(Q₅₁)(Q₅₂)(Q₅₃), or —Ge(Q₅₁)(Q₅₂)(Q₅₃),

Q₅₁ to Q₅₃ may each independently be a C₁-C₂₀ alkyl group,

R₃₁ to R₃₄ may each independently be the same as described in connectionwith R₃₀,

R₄₁ to R₄₄ may each independently be the same as described in connectionwith R₄₀, and

* to *′ each indicate a binding site to M₁.

In one or more embodiments, the organometallic compound may not includean amine group.

Although not wishing to be limited by a specific theory, when an aminegroup is substituted on A₂ which is a moiety related to a lowestunoccupied molecular orbital (LUMO) energy level of the organometalliccompound represented by Formula 1, the electron donating effectincreases. Accordingly, the emission wavelength of the organometalliccompound may become longer, making it difficult to exhibit a desiredemission wavelength with high color purity (for example, an emissionwavelength of pure green). In addition, since the amine group exhibitsmelting characteristics during a deposition process of theorganometallic compound, such a material may be highly susceptible todeterioration, resulting in deterioration of characteristics of a formedorganic light-emitting device.

In the present specification, TMS represents *—Si(CH₃)₃, and TMGrepresents * —Ge(CH₃)₃.

In one or more embodiments, the organometallic compound represented byFormula 1 may be a compound represented by one of Compounds 1 to 36:

wherein, in Formula 1, at least one of R₁, R₂, and R₃ may be a grouprepresented by Formula 1-1. In addition, when A, in Formula 1A is abenzene group, (i) at least one of R₂₀(s) in the number of b20 may be asubstituted or unsubstituted C₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃), or (ii) R₁ or R₂ may be a group represented by Formula1-1.

Without wishing to be bound to theory, by introducing a structure inwhich a hetero group (e.g., a carbazole group) capable of supplyingabundant pi electrons to A₁, which is a moiety related to a highestoccupied molecular orbital (HOMO) energy level in the ligand representedby Formula 1A, is condensed to the organometallic compound representedby Formula 1, an organic light-emitting device using the organometalliccompound may have high luminescence efficiency and excellent thermalstability.

Accordingly, an electronic device, for example, an organiclight-emitting device, including the organometallic compound representedby Formula 1 may exhibit a low driving voltage, high efficiency, a longlifespan, and a reduced roll-off phenomenon.

The HOMO energy level (electron volts, eV), LUMO energy level (eV), S₁energy level (eV), and T₁ energy level (eV) of some compounds of theorganometallic compound represented by Formula 1 were evaluated usingthe Gaussian 09 program with the molecular structure optimizationobtained by B3LYP-based density functional theory (DFT), and resultsthereof are shown in Table 1.

TABLE 1 Compound No. HOMO (eV) LUMO (eV) S₁ (eV) T₁ (eV) Compound 1−4.868 −1.341 2.883 2.563 Compound 3 −4.942 −1.398 2.850 2.487 Compound4 −4.938 −1.402 2.836 2.476 Compound 20 −4.946 −1.365 2.882 2.504Compound C −4.866 −1.607 2.800 2.535 Compound D −4.896 −1.502 2.8292.553

 

 

 

 

 

From Table 1, it is confirmed that the organometallic compoundrepresented by Formula 1 has such electric characteristics that aresuitable for use as a dopant for an electric device, for example, anorganic light-emitting device.

In one or more embodiments, the full width at half maximum (FWHM) of theemission peak of the emission spectrum or the electroluminescencespectrum of the organometallic compound may be equal to or less thanabout 55 nanometers (nm). For example, the FWHM of the emission peak ofthe emission spectrum or the electroluminescence spectrum of theorganometallic compound may be from about 30 nm to about 55 nm, about 40nm to about 53 nm, or about 45 nm to about 52 nm.

In one or more embodiments, the maximum emission wavelength (emissionpeak wavelength, λ_(max)) of the emission peak of the emission spectrumor the electroluminescence spectrum of the organometallic compound maybe from about 500 nm to about 600 nm.

Synthesis methods of the organometallic compound represented by Formula1 may be recognizable by one of ordinary skill in the art by referringto Synthesis Examples provided below.

In this regard, the organometallic compound represented by Formula 1 maybe suitable for use in an organic layer of an organic light-emittingdevice, for example, for use as a dopant in an emission layer of theorganic layer. Thus, another aspect of the present disclosure providesan organic light-emitting device including: a first electrode; a secondelectrode; and an organic layer arranged between the first electrode andthe second electrode and including an emission layer and at least oneorganometallic compound represented by Formula 1.

Since the organic light-emitting device has an organic layer includingthe organometallic compound represented by Formula 1 as described above,excellent characteristics may be obtained with respect to drivingvoltage, current efficiency, external quantum efficiency, a roll-offratio, and lifespan, and the FWHM of the emission peak of the ELspectrum may be relatively narrow.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of the organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may act as adopant, and the emission layer may further include a host (that is, anamount of the organometallic compound represented by Formula 1 in theemission layer is smaller than that of the host).

In one or more embodiments, the emission layer may emit green light. Forexample, the emission layer may emit green light having a maximumluminescence wavelength from about 500 nm to about 600 nm.

The expression “(an organic layer) includes at least one oforganometallic compounds” as used herein may include a case in which“(an organic layer) includes identical organometallic compoundsrepresented by Formula 1” and a case in which “(an organic layer)includes two or more different organometallic compounds represented byFormula 1.”

In one or more embodiments, the organic layer may include, as theorganometallic compound, only Compound 1. In this embodiment, Compound 1may be included in the emission layer of the organic light-emittingdevice. In one or more embodiments, the organic layer may include, asthe organometallic compound, Compound 1 and Compound 2. In thisembodiment, Compound 1 and Compound 2 may exist in an identical layer(for example, Compound 1 and Compound 2 all may exist in an emissionlayer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode; or the first electrode may be a cathode,which is an electron injection electrode, and the second electrode maybe an anode, which is a hole injection electrode.

For example, in the organic light-emitting device, the first electrodemay be an anode, and the second electrode may be a cathode, and theorganic layer may further include a hole transport region between thefirst electrode and the emission layer and an electron transport regionbetween the emission layer and the second electrode, wherein the holetransport region may include a hole injection layer, a hole transportlayer, an electron blocking layer, a buffer layer, or any combinationthereof, and the electron transport region may include a hole blockinglayer, an electron transport layer, an electron injection layer, or anycombination thereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. The “organic layer” mayinclude, in addition to an organic compound, an organometallic complexincluding metal.

FIGURE is a schematic cross-sectional view of an organic light-emittingdevice 10 according to one or more embodiments. Hereinafter, thestructure of an organic light-emitting device according to one or moreembodiments of the present disclosure and a method of manufacturing anorganic light-emitting device according to one or more embodiments ofthe present disclosure will be described in connection with FIGURE. Theorganic light-emitting device 10 includes a first electrode 11, anorganic layer 15, and a second electrode 19, which are sequentiallystacked.

A substrate may be additionally arranged under the first electrode 11 orabove the second electrode 19. For use as the substrate, any substratethat is used in organic light-emitting devices available in the art maybe used, and the substrate may be a glass substrate or a transparentplastic substrate, each having excellent mechanical strength, thermalstability, transparency, surface smoothness, ease of handling, and waterresistance.

In one or more embodiments, the first electrode 11 may be formed bydepositing or sputtering a material for forming the first electrode 11on the substrate.

The first electrode 11 may be an anode. The material for forming thefirst electrode 11 may include materials with a high work function tofacilitate hole injection. The first electrode 11 may be a reflectiveelectrode, a semi-transmissive electrode, or a transmissive electrode.In one or more embodiments, the material for forming the first electrode11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide(SnO₂), or zinc oxide (ZnO). In one or more embodiments, the materialfor forming the first electrode 11 may be metal, such as magnesium (Mg),aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium(Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or amulti-layered structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO.

The organic layer 15 is arranged on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be arranged between the first electrode 11and the emission layer.

The hole transport region may include a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or anycombination thereof.

In one or more embodiments, the hole transport region may include onlyeither a hole injection layer or a hole transport layer. In one or moreembodiments, the hole transport region may have a hole injectionlayer/hole transport layer structure or a hole injection layer/holetransport layer/electron blocking layer structure, wherein, layers ineach structure are sequentially stacked in this stated order from thefirst electrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using one ormore suitable methods, for example, vacuum deposition, spin coating,casting, and/or Langmuir-Blodgett (LB) deposition.

When the hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a compound that is used as amaterial for forming the hole injection layer, and the structure andthermal characteristics of the hole injection layer. For example, thedeposition conditions may include a deposition temperature in a range ofabout 100° C. to about 500° C., a vacuum pressure in a range of about10-8 torr to about 10-3 torr, and a deposition rate in a range of about0.01 Å/sec to about 100 Å/sec. However, the deposition conditions arenot limited thereto.

When the hole injection layer is formed by spin coating, the coatingconditions may vary according to a compound that is used as a materialfor forming the hole injection layer, and the structure and thermalproperties of the hole injection layer. For example, the coatingconditions may include a coating speed in a range of about 2,000 rpm toabout 5,000 rpm, and a temperature at which a heat treatment isperformed to remove a solvent after coating may be in a range of about80° C. to about 200° C. However, the coating conditions are not limitedthereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer.

The hole transport region may include, for example, m-MTDATA, TDATA,2-TNATA, NPB, R-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC,HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS),poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine)](TFB), a compound represented by Formula 201, a compound represented byFormula 202, or any combination thereof:

In Formula 201, Ar₁₀₁ and Ar₁₀₂ may each independently be a phenylenegroup, a pentalenylene group, an indenylene group, a naphthylene group,an azulenylene group, a heptalenylene group, an acenaphthylene group, afluorenylene group, a phenalenylene group, a phenanthrenylene group, ananthracenylene group, a fluoranthenylene group, a triphenylenylenegroup, a pyrenylene group, a chrysenylenylene group, a naphthacenylenegroup, a picenylene group, a perylenylene group, or a pentacenylenegroup, each unsubstituted or substituted with one or more of deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, aC₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, a C₂-C₆₀alkylheteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, or a monovalent non-aromatic condensed heteropolycyclic group.

In Formula 201, xa and xb may each independently be an integer from 0 to5, or 0, 1, or 2. For example, xa may be 1, and xb may be 0, butembodiments are not limited thereto.

In Formulae 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, a propyl group, abutyl group, a pentyl group, a hexyl group, or the like), or a C₁-C₁₀alkoxy group (for example, a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, a pentoxy group, or the like);

a C₁-C₁₀ alkyl group or a C₁-C₁₀ alkoxy group, each unsubstituted orsubstituted with one or more of deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, or a phosphoric acid or a saltthereof; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, or a pyrenyl group, each unsubstituted or substituted with one ormore of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₁₀ alkylgroup, or a C₁-C₁₀ alkoxy group.

In Formula 201, R₁₀₉ may be a phenyl group, a naphthyl group, ananthracenyl group, or a pyridinyl group, each unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthracenyl group, a pyridinyl group, or any combinationthereof.

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A:

wherein, in Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ may each be thesame as described herein.

For example, the hole transport region may include one or more ofCompounds HT1 to HT21, or any combination thereof:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one of a hole injection layerand a hole transport layer, a thickness of the hole injection layer maybe in a range of about 100 Å to about 10,000 Å, for example, about 100 Åto about 1,000 Å, and a thickness of the hole transport layer may be ina range of about 50 Å to about 2,000 Å, for example, about 100 Å toabout 1,500 Å. When the thicknesses of the hole transport region, thehole injection layer, and the hole transport layer are within theseranges, satisfactory hole transporting characteristics may be obtainedwithout a substantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may include a quinone derivative, a metal oxide, a cyanogroup-containing compound, or any combination particular, butembodiments of the present disclosure are not limited thereto. Forexample, the p-dopant may be: a quinone derivative such astetracyanoquinodimethane (TCNQ),2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), orF6-TCNNQ; metal oxide, such as tungsten oxide and molybdenum oxide; acyano group-containing compound, such as Compound HT-D1 or F12; or anycombination thereof.

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for forming the electron blocking layer may include amaterial that is used in the hole transport region as described above, ahost material described below, or any combination thereof. For example,when the hole transport region includes an electron blocking layer, mCP,Compound HT21, or any combination may be used as the material forforming the electron blocking layer.

Then, the emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied informing the hole injection layer although the deposition or coatingconditions may vary according to a material that is used to form thehole transport layer.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1 asdescribed herein.

The host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP,CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, Compound 53,Compound 54, or any combination thereof:

In one or more embodiments, when the organic light-emitting device is afull-color organic light-emitting device, the emission layer may bepatterned into a red emission layer, a green emission layer, and/or ablue emission layer. In one or more embodiments, due to a stackedstructure including a red emission layer, a green emission layer, and/ora blue emission layer, the emission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 parts by weight to about 15 partsby weight based on 100 parts by weight of the host, but embodiments ofthe present disclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within these ranges, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be arranged on the emissionlayer.

The electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

For example, the electron transport region may have a hole blockinglayer/electron transport layer/electron injection layer structure or anelectron transport layer/electron injection layer structure. Theelectron transport layer may have a single-layered structure or amulti-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP,Bphen, and BAlq.

The hole blocking layer may include the host, a material for forming anelectron transport layer, a material for forming an electron injectionlayer, which will be described later, or any combination thereof.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 600 Å. When thethickness of the hole blocking layer is within these ranges, excellenthole blocking characteristics may be obtained without a substantialincrease in driving voltage.

In one or more embodiments, the electron transport layer may includeBCP, Bphen, TPBi, Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

In one or more embodiments, the electron transport layer may include atleast one of Compounds ET1 to ET25, or any combination thereof:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within these ranges,satisfactory electron transport characteristics may be obtained withouta substantial increase in driving voltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 or ET-D2:

In addition, the electron transport region may include an electroninjection layer that promotes the flow of electrons from the secondelectrode 19 thereinto.

The electron injection layer may include LiF, NaCl, CsF, Li₂O, BaO, orany combination thereof.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within these ranges,satisfactory electron injection characteristics may be obtained withouta substantial increase in driving voltage.

The second electrode 19 is arranged on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be metal, an alloy, an electrically conductivecompound, or a combination thereof, which have a relatively low workfunction. For example, the material for forming the second electrode 19may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver(Mg—Ag).

To manufacture a top-emission type light-emitting device, a transmissiveelectrode formed using ITO or IZO may be used as the material forforming the second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to the FIGURE, but embodiments of the present disclosure arenot limited thereto.

In one or more embodiments, the organic light-emitting device may beincluded in an electronic apparatus. Thus, another aspect of the presentdisclosure provides an electronic apparatus including the organiclight-emitting device. The electronic apparatus may include, forexample, a display, an illumination, a sensor, and the like.

Another aspect of the present disclosure provides a diagnosticcomposition including at least one organometallic compound representedby Formula 1.

The organometallic compound represented by Formula 1 provides highluminescent efficiency. Accordingly, the diagnostic compositionincluding the organometallic compound may have high diagnosticefficiency.

The diagnostic composition may be used in various applications includinga diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched saturated aliphatic hydrocarbons monovalent group having 1 to60 carbon atoms, and the term “C₁-C₆₀ alkylene group” as used hererefers to a divalent group having the same structure as the C₁-C₆₀ alkylgroup.

Examples of the C₁-C₆₀ alkyl group, the C₁-C₂₀ alkyl group, and/or theC₁-C₁₀ alkyl group are a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a sec-butyl group, anisobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentylgroup, a neopentyl group, an isopentyl group, a sec-pentyl group, a3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexylgroup, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, anisoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octylgroup, an isooctyl group, a sec-octyl group, a tert-octyl group, ann-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group,an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decylgroup, each unsubstituted or substituted with a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, asec-butyl group, an isobutyl group, a tert-butyl group, an n-pentylgroup, a tert-pentyl group, a neopentyl group, an isopentyl group, asec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexylgroup, an isohexyl group, a sec-hexyl group, a tert-hexyl group, ann-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an isooctyl group, a sec-octyl group, atert-octyl group, an n-nonyl group, an isononyl group, a sec-nonylgroup, a tert-nonyl group, an n-decyl group, an isodecyl group, asec-decyl group, a tert-decyl group, or any combination thereof. Forexample, Formula 9-33 is a branched C alkyl group, for example, atert-butyl group that is substituted with two methyl groups.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof are a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, and a pentoxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup formed by substituting at least one carbon-carbon double bond inthe middle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof are an ethenyl group, a propenyl group, and a butenyl group. Theterm “C₂-C₆₀ alkenylene group” as used herein refers to a divalent grouphaving the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup formed by substituting at least one carbon-carbon triple bond inthe middle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof are an ethynyl group and a propynyl group. The term “C₁-C₆alkynylene group” as used herein refers to a divalent group having thesame structure as the C₁-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andthe term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

Examples of the C₃-C₁₀ cycloalkyl group are a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a bicyclo[1.1.1]pentylgroup, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl(norbornanyl)group, a bicyclo[2.2.2]octyl group, and the like.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonocyclic group that includes at least one heteroatom selected from N,O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms, and theterm “C₁-C₁₀ heterocycloalkylene group” as used herein refers to adivalent group having the same structure as the C₁-C₁₀ heterocycloalkylgroup.

Examples of the C₁-C₁₀ heterocycloalkyl group are a silolanyl group, asilinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group,and a tetrahydrothiophenyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and examples thereof are a cyclopentenyl group, a cyclohexenyl group,and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” asused herein refers to a divalent group having the same structure as theC₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Examples of theC₁-C₁₀ heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Examples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the two or more rings may be fused toeach other.

The term “C₇-C₆₀ alkylaryl group” as used herein refers to a C₆-C₆₀ arylgroup substituted with at least one C₁-C₆₀ alkyl group.

The term “C₁-C₆ heteroaryl group” as used herein refers to a monovalentgroup having at least one hetero atom selected from N, O, P, Si, and Sas a ring-forming atom and a cyclic aromatic system having 1 to 60carbon atoms, and the term “C₁-C₆₀ heteroarylene group” as used hereinrefers to a divalent group having at least one hetero atom selected fromN, O, P, Si, and S as a ring-forming atom and a carbocyclic aromaticsystem having 1 to 60 carbon atoms. Examples of the C₁-C₆₀ heteroarylgroup are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, and anisoquinolinyl group.

When the C₆-C₆₀ heteroaryl group and the C₆-C₆₀ heteroarylene group eachinclude two or more rings, the two or more rings may be fused to eachother.

The term “C₂-C₆₀ alkylheteroaryl group used herein refers to a C₁-C₆₀heteroaryl group substituted with at least one C₁-C₆₀ alkyl group.

The term “C₆-C₆₀ aryloxy group” as used herein indicates —OA₁₀₂ (whereinA₁₀₂ indicates the C₆-C₆₀ aryl group), the term “C₆-C₆₀ arylthio group”as used herein indicates —SA₁₀₃ (wherein A₁₀₃ indicates the C₆-C₆₀ arylgroup), and the term “C₁-C₆ alkylthio group” as used herein indicates—SA₁₀₄ (wherein A₁₀₄ indicates the C₁-C₆₀ alkyl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. An example of the monovalent non-aromatic condensedpolycyclic group is a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as a monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) having two or more rings condensed to each other, aheteroatom selected from N, O, P, Si, and S, other than carbon atoms, asa ring-forming atom, and no aromaticity in its entire molecularstructure. An example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. The term “divalentnon-aromatic heterocondensed polycyclic group” as used herein refers toa divalent group having the same structure as a monovalent non-aromaticheterocondensed polycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturatedor unsaturated cyclic group having, as a ring-forming atom, 5 to 30carbon atoms only.

The C₅-C₃₀ carbocyclic group may be a monocyclic group or a polycyclicgroup.

Examples of the “C₅-C₃₀ carbocyclic group (unsubstituted or substitutedwith at least one R_(1a))” are an adamantane group, a norbornene group,a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, abicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, acyclopentane group, a cyclohexane group, a cyclohexene group, a benzenegroup, a naphthalene group, an anthracene group, a phenanthrene group, atriphenylene group, a pyrene group, a chrysene group, a1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a silolegroup, and a fluorene group (, each unsubstituted or substituted with atleast one R_(1a)).

The term “C₁-C₃₀ heterocyclic group” as used herein refers to asaturated or unsaturated cyclic group having, as a ring-forming atom, atleast one heteroatom selected from N, O, P, Si, Se, Ge, B, and S otherthan 1 to 30 carbon atoms. The C₁-C₆₀ heterocyclic group may be amonocyclic group or a polycyclic group. Examples of the “C₁-C₃₀heterocyclic group (unsubstituted or substituted with at least oneR_(1a))” are a thiophene group, a furan group, a pyrrole group, a silolegroup, borole group, a phosphole group, a selenophene group, a germolegroup, a benzothiophene group, a benzofuran group, an indole group, anindene group, a benzosilole group, a benzoborole group, a benzophospholegroup, a benzoselenophene group, a benzogermole group, adibenzothiophene group, a dibenzofuran group, a carbazole group, adibenzosilole group, a dibenzoborole group, a dibenzophosphole group, adibenzoselenophene group, a dibenzogermole group, a dibenzothiophene5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxidegroup, an azabenzothiophene group, an azabenzofuran group, an azaindolegroup, an azaindene group, an azabenzosilole group, an azabenzoborolegroup, an azabenzophosphole group, an azabenzoselenophene group, anazabenzogermole group, an azadibenzothiophene group, an azadibenzofurangroup, an azacarbazole group, an azafluorene group, an azadibenzosilolegroup, an azadibenzoborole group, an azadibenzophosphole group, anazadibenzoselenophene group, an azadibenzogermole group, anazadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, anazadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, aquinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a phenanthroline group, a pyrazole group, animidazole group, a triazole group, an oxazole group, an isooxazolegroup, a thiazole group, an isothiazole group, an oxadiazole group, athiadiazole group, a benzopyrazole group, a benzimidazole group, abenzoxazole group, a benzothiazole group, a benzoxadiazole group, abenzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a5,6,7,8-tetrahydroquinoline group (, each unsubstituted or substitutedwith at least one R_(1a)).

The terms “fluorinated C₁-C₆₀ alkyl group (or a fluorinated C₁-C₂₀ alkylgroup or the like)”, “fluorinated C₃-C₁₀ cycloalkyl group”, “fluorinatedC₁-C₁₀ heterocycloalkyl group,” and “fluorinated phenyl group”respectively indicate a C₁-C₆₀ alkyl group (or a C₁-C₂₀ alkyl group orthe like), a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group,and a phenyl group, each substituted with at least one fluoro group(—F). For example, the “fluorinated C₁ alkyl group (that is, thefluorinated methyl group)” may include —CF₃, —CF₂H, and —CFH₂. The“fluorinated C₁-C₆₀ alkyl group (or, a fluorinated C₁-C₂₀ alkyl group,or the like)”, “the fluorinated C₃-C₁₀ cycloalkyl group”, “thefluorinated C₁-C₁₀ heterocycloalkyl group”, or “the fluorinated a phenylgroup” may be i) a fully fluorinated C₁-C₆₀ alkyl group (or, a fullyfluorinated C₁-C₂₀ alkyl group, or the like), a fully fluorinated C₃-C₁₀cycloalkyl group, a fully fluorinated C₁-C₁₀ heterocycloalkyl group, ora fully fluorinated phenyl group, wherein, in each group, all hydrogenincluded therein is substituted with a fluoro group, or ii) a partiallyfluorinated C₁-C₆₀ alkyl group (or, a partially fluorinated C₁-C₂₀ alkylgroup, or the like), a partially fluorinated C₃-C₁₀ cycloalkyl group, apartially fluorinated C₁-C₁₀ heterocycloalkyl group, or partiallyfluorinated phenyl group, wherein, in each group, each hydrogen includedtherein is not substituted with a fluoro group.

The terms “deuterated C₁-C₆₀ alkyl group (or a deuterated C₁-C₂₀ alkylgroup or the like)”, “deuterated C₃-C₁₀ cycloalkyl group”, “deuteratedC₁-C₁₀ heterocycloalkyl group,” and “deuterated phenyl group”respectively indicate a C₁-C₆₀ alkyl group (or a C₁-C₂₀ alkyl group orthe like), a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group,and a phenyl group, each substituted with at least one deuterium. Forexample, the “deuterated C₁ alkyl group (that is, the deuterated methylgroup)” may include —CD₃, —CD₂H, and —CDH₂, and examples of the“deuterated C₃-C₁₀ cycloalkyl group” are, for example, Formula 10-501and the like. The “deuterated C₁-C₆₀ alkyl group (or, the deuteratedC₁-C₂₀ alkyl group or the like)”, “the deuterated C₃-C₁₀ cycloalkylgroup”, “the deuterated C₁-C₁₀ heterocycloalkyl group”, or “thedeuterated phenyl group” may be i) a fully deuterated C₁-C₆₀ alkyl group(or, a fully deuterated C₁-C₂₀ alkyl group or the like), a fullydeuterated C₃-C₁₀ cycloalkyl group, a fully deuterated C₁-C₁₀heterocycloalkyl group, or a fully deuterated phenyl group, in which, ineach group, all hydrogen included therein are substituted withdeuterium, or ii) a partially deuterated C₁-C₆₀ alkyl group (or, apartially deuterated C₁-C₂₀ alkyl group or the like), a partiallydeuterated C₃-C₁₀ cycloalkyl group, a partially deuterated C₁-C₁₀heterocycloalkyl group, or a partially deuterated phenyl group, inwhich, in each group, each hydrogen included therein is not substitutedwith deuterium.

The term “(C₁-C₂₀ alkyl) ‘X’ group” as used herein refers to a ‘X’ groupthat is substituted with at least one C₁-C₂₀ alkyl group. For example,the term “(C₁-C₂₀ alkyl)C₃-C₁₀ cycloalkyl group” as used herein refersto a C₃-C₁₀ cycloalkyl group substituted with at least one C₁-C₂₀ alkylgroup, and the term “(C₁-C₂₀ alkyl)phenyl group” as used herein refersto a phenyl group substituted with at least one C₁-C₂₀ alkyl group. Anexample of a (C₁ alkyl) phenyl group is a toluyl group.

The terms “an azaindole group, an azabenzoborole group, anazabenzophosphole group, an azaindene group, an azabenzosilole group, anazabenzogermole group, an azabenzothiophene group, anazabenzoselenophene group, an azabenzofuran group, an azacarbazolegroup, an azadibenzoborole group, an azadibenzophosphole group, anazafluorene group, an azadibenzosilole group, an azadibenzogermolegroup, an azadibenzothiophene group, an azadibenzoselenophene group, anazadibenzofuran group, an azadibenzothiophene 5-oxide group, anaza-9H-fluoren-9-one group, an azadibenzothiophene group, or a5,5-dioxide group” as used herein respectively refer to heterocyclicgroups having the same backbones as “an indole group, a benzoborolegroup, a benzophosphole group, an indene group, a benzosilole group, abenzogermole group, a benzothiophene group, a benzoselenophene group, abenzofuran group, a carbazole group, a dibenzoborole group, adibenzophosphole group, a fluorene group, a dibenzosilole group, adibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a9H-fluoren-9-one group, a dibenzothiophene group, or a 5,5-dioxidegroup,” in which, in each group, at least one carbon selected fromring-forming carbons is substituted with nitrogen.

At least one substituent of the substituted C₅-C₃₀ carbocyclic group,the substituted C₂-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₁-C₆₀ alkylthio group, the substituted C₃-C₁₀ cycloalkyl group, thesubstituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, thesubstituted C₆-C₆₀ aryl group, the substituted C₇-C₆₀ alkylaryl group,the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthiogroup, the substituted C₇-C₆₀ arylalkyl group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀ heteroaryloxy group, thesubstituted C₁-C₆₀ heteroarylthio group, the substituted C₂-C₆₀heteroarylalkyl group, the substituted C₂-C₆₀ alkylheteroaryl group, thesubstituted C₂-C₆₀ alkyl heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may each independently be:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, or a C₁-C₆₀ alkylthio group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, or a C₁-C₆₀ alkylthio group, substituted with oneor more of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group,a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, aC₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀heteroarylalkyl group, a C₂-C₆₀ alkylheteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅),—Ge(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or —P(Q₁₈)(Q₁₉); aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, aC₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀heteroarylalkyl group, a C₂-C₆₀ alkylheteroaryl group, a monovalentnon-aromatic condensed polycyclic group, or a monovalent non-aromaticcondensed heteropolycyclic group, each unsubstituted or substituted withone or more of deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₁-C₆₀ alkylthio group C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkylaryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, aC₂-C₆₀ alkylheteroaryl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —Ge(Q₂₃)(Q₂₄)(Q₂₅),—B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or —P(Q₂₈)(Q₂₉);

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —Ge(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇),—P(═O)(Q₃₈)(Q₃₉), or —P(Q₃₈)(Q₃₉); or

any combination thereof.

In the present specification, Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁to Q₃₉ may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I;a hydroxyl group; a cyano group; a nitro group; an amidino group; ahydrazine group; a hydrazone group; a carboxylic acid or a salt thereof;a sulfonic acid or a salt thereof; a phosphoric acid or a salt thereof;a C₁-C₆₀ alkyl group which is unsubstituted or substituted withdeuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combinationthereof; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxygroup; a C₁-C₆₀ alkylthio group; a C₃-C₁₀ cycloalkyl group; a C₁-C₁₀heterocycloalkyl group; a C₃-C₁₀ cycloalkenyl group; a C₁-C₁₀heterocycloalkenyl group; a C₆-C₆₀ aryl group which is unsubstituted orsubstituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group,or any combination thereof; a C₆-C₆₀ aryloxy group; a C₆-C₆₀ arylthiogroup; a C₇-C₆₀ arylalkyl group; a C₁-C₆₀ heteroaryl group; a C₁-C₆₀heteroaryloxy group; a C₁-C₆₀ heteroarylthio group; a C₂-C₆₀heteroarylalkyl group; a C₂-C₆₀ alkylheteroaryl group; a monovalentnon-aromatic condensed polycyclic group; or a monovalent non-aromaticcondensed heteropolycyclic group.

For example, Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ describedherein may each independently be:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃,—CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH₂; or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an n-pentyl group, atert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentylgroup, a 3-pentyl group, a sec-isopentyl group, a phenyl group, abiphenyl group, or a naphthyl group, each unsubstituted or substitutedwith deuterium, a C₁-C₁₀ alkyl group, or a phenyl group,

or any combination thereof.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the present disclosure is not limitedthereto. The wording “‘B’ was used instead of ‘A’” used in describingSynthesis Examples means that an amount of ‘A’ used was identical to anamount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES Synthesis Example 1: (Synthesis of Compound 1)

(1) Synthesis of Compound 1A

2-phenyl-pyridine (5.2 grams (g), 33.1 millimoles (mmol)) and iridiumchloride (5.2 g, 14.7 mmol) were mixed with 120 milliliters (mL) ofethoxyethanol and 40 mL of deionized water (DI water), and the resultantmixed solution was stirred under reflux for 24 hours. Then, the reactiontemperature was lowered to room temperature. A solid produced therefromwas separated by filtration, washed thoroughly withwater/methanol/hexane in this stated order, and dried in a vacuum oven,so as to obtain 8.2 g (yield of 92%) of Compound 1 Å. Compound 1 Å wasused in the next reaction without performing any additional purificationprocess thereon.

(2) Synthesis of Compound 1B

Compound 1 Å (1.6 g, 1.5 mmol) was mixed with 45 mL of methylenechloride, and a mixture of silver triflate (AgOTf) (0.8 g, 3.1 mmol) and15 mL of methanol were added thereto. Afterwards, the resultant mixedsolution was stirred for 18 hours while blocking light with aluminumfoil, and then, filtered through celite to remove the resultant solid.The filtrate was decompressed to obtain a solid (Compound 1B), which wasused in the next reaction without performing any additional purificationprocess thereon.

(3) Synthesis of Compound 2A

In a nitrogen environment, 9-(4-bromophenyl)-9H-carbazole (1.5 g, 4.66mmol), bis(pinacolato)diboron (1.54 g, 6.05 mmol),[1,1-bis(diphenylphosphineo)-ferrocene]palladium(II) dichloride (0.34 g,0.47 mmol), and potassium acetate (1.37 g, 13.97 mmol) were added to a1,4-dioxane/toluene (1:1) solvent and stirred. The mixed solution wasstirred in an oil bath at a temperature of 120° C. for 17 hours. Aftercompletion of the reaction, the reaction temperature was cooled to roomtemperature, the solvent was removed, and the obtained solid wassubjected to column chromatography (eluent:methylene chloride (MC) andhexane), so as to obtain 1.6 g (yield of 93%) of9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolane-2-yl)phenyl)-9H-carbazole.The obtained material was identified by HRMS and HPLC analysis.

High resolution mass spectrometry (matrix assisted laser desorptionionization) (HRMS (MALDI)) calcd for C₂₄H₂₄BNO₂: m/z: 369.19 Found:370.23.

(4) Synthesis of Compound 2B

In a nitrogen environment, 2-bromo-4-isobutyl-5-(trimethylsilyl)pyridine(1.5 g, 5.24 mmol) was dissolved in 100 mL of tetrahydrofuran, and9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)phenyl)-9H-carbazole(Compound 1 Å) (2.1 g, 5.76 mmol) was added thereto. Potassium carbonate(K₂CO₃) (1.7 g, 15.72 mmol) was dissolved in 25 mL of DI water and addedto the reaction mixture. A palladium catalyst (Pd(PPh₃)₄) (0.6 g, 0.52mmol) was then added thereto. Then, the resultant reaction mixture wasstirred at reflux at a temperature of 80° C. Following an extractionprocess, the obtained solid was subjected to column chromatography(eluent: MC and hexane), so as to obtain 1.91 g (yield of 92%) of9-(4-(4-isobutyl-5-(trimethylsilyl)pyridin-2-yl)phenyl)-9H-carbazole.The obtained material was identified by HRMS and high-performance liquidchromatography (HPLC) analysis.

HRMS(MALDI) calcd for C₃₀H₃₂N₂Si: m/z: 448.23 Found: 449.69.

(5) Synthesis of Compound 1

Compound 1B (1.5 g, 2.10 mmol) and9-(4-(4-isobutyl-5-(trimethylsilyl)pyridin-2-yl)phenyl)-9H-carbazole(Compound 2B) (1.0 g, 2.31 mmol) were mixed with 40 mL of2-ethoxyethanol, and the resultant mixed solution was stirred at atemperature of 110° C. for 24 hours. Then, the reaction temperature wasreduced. The resultant mixture was decompressed, and the obtained solidwas subjected to column chromatography (eluent:methylene chloride andhexanes), to obtain 0.93 g (yield of 47%) of Compound 1. The obtainedmaterial was identified by HRMS and HPLC analysis.

HRMS(MALDI) calcd for C₅₂H₄₇IrN₄Si: m/z: 948.32 Found: 949.28.

Synthesis Example 2: (Synthesis of Compound 3)

(1) Synthesis of Compound 3A

In a nitrogen environment, (1-chlorodibenzo[b,d]furan-4-yl)boronic acid(3.0 g, 10.5 mmol) and 2-bromo-4-isobutyl-5-(trimethylsilyl)pyridine(3.1 g, 12.6 mmol) were dissolved in 200 mL of tetrahydrofuran. K₂CO₃(3.3 g, 31.4 mmol) was dissolved in 50 mL of DI water and added to thereaction mixture. Then, a palladium catalyst (Pd(PPh₃)₄) (1.2 g, 1.05mmol) was added thereto. Next, the resultant reaction mixture wasstirred at reflux at a temperature of 100° C. Following an extractionprocess, the obtained solid was subjected to column chromatography(eluent: MC and hexane), so as to obtain 3.9 g (yield of 95%) of2-(1-chlorodibenzo[b,d]furan-4-yl)-4-isobutyl-5-(trimethylsilyl)pyridine.The obtained material was identified by HRMS and HPLC analysis.

HRMS (MALDI) calcd for C₂₄H₂₆ClNOSi: m/z: 407.15 Found: 409.20.

(2) Synthesis of Compound 3B

In a nitrogen environment, Compound 3 Å (6.1 g, 14.9 mmol), 9H-carbazole(1.0 g, 6.0 mmol), sodium t-butoxide (1.2 g, 11.9 mmol), andbis(tri-t-butylphosphine)palladium(0) (610 mg, 1.2 mmol) were added to50 mL of toluene, and stirred at reflux. After completion of thereaction, the reaction temperature was cooled to room temperature, andan extraction process was performed using methylene chloride and water.After treatment with anhydrous magnesium sulfate, the resultant productwas filtered and concentrated under reduced pressure. Following anextraction process, the obtained solid was subjected to columnchromatography (eluent:methylene chloride and hexanes), to obtain 2.7 g(yield of 84%) of9-(4-(4-isobutyl-5-(trimethylsilyl)pyridin-2-yl)dibenzo[b.d]furan-1-yl)-9H-carbazole.The obtained material was identified by HRMS and HPLC analysis.

HRMS (MALDI) calcd for C₃₆H₃₄N₂OSi: m/z: 538.24 Found: 539.78.

(3) Synthesis of Compound 3

Compound 1B (1.5 g, 2.1 mmol) and Compound 3B (1.3 g, 2.3 mmol) werecombined with 20 mL of 2-ethoxyethanol and 20 mL ofN,N-dimethylformamide, and the resultant mixed solution was stirred at atemperature of 110° C. for 24 hours. Then, the reaction temperature wasreduced. An extraction process was performed using methylene chlorideand water. After treatment with anhydrous magnesium sulfate, theresultant product was filtered and concentrated under reduced pressure.Following the extraction process, the obtained solid was subjected tocolumn chromatography (eluent:methylene chloride and hexanes), to obtain0.8 g (yield of 38%) of Compound 3. The obtained material was identifiedby HRMS and HPLC analysis.

HRMS (MALDI) calcd for C₅₈H₄₉IrN₄OSi: m/z: 1038.33 Found: 1039.40.Synthesis Example 3: (Synthesis of Compound 4)

0.8 g (yield of 36%) of Compound 4 was obtained in the same manner as inthe synthesis of Compound 3, except that, instead of(1-chlorodibenzo[b,d]furan-4-yl)boronic acid,1-chlorodibenzo[b,d]thiophen-4-yl)boronic acid was used as a startingmaterial in synthesizing Compound 3A so as to synthesize Compound 4A.The obtained material was identified by HRMS and HPLC analysis.

HRMS (MALDI) calcd for C₅₈H₄₉IrN₄SSi: m/z: 1054.31 Found: 1055.48

Synthesis Example 4: (Synthesis of Compound 5)

0.9 g (yield of 44%) of Compound 5 was obtained in the same manner as inthe synthesis of Compound 3, except that, instead of2-bromo-4-isobutyl-5-(trimethylsilyl)pyridine,2-bromo-4-isopropylpyridine was used as a starting material insynthesizing Compound 3A so as to synthesize Compound 5A. The obtainedmaterial was identified by HRMS and HPLC analysis.

HRMS (MALDI) calcd for C₅₄H₃₉IrN₄O: m/z: 952.28 Found: 953.15

Example 1

As an anode, an ITO-patterned glass substrate was cut to a size of 50mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water each for5 minutes, and then cleaned by exposure to ultraviolet rays and ozonefor 30 minutes. The resultant glass substrate was loaded onto a vacuumdeposition apparatus.

Compounds HT3 and F12 (p-dopant) were vacuum co-deposited on the anodeat a weight ratio of 98:2 to form a hole injection layer having athickness of 100 Å, and Compound HT3 was vacuum deposited on the holeinjection layer to form a hole transport layer having a thickness of1,650 Å.

Sub sequentially, Compound GH3 (host) and Compound 1 (dopant) wereco-deposited at a weight ratio of 92:8 on the hole transport layer toform an emission layer having a thickness of 400 Å.

Next, Compound ET3 and LiQ (n-dopant) were co-deposited at a volumeratio of 50:50 on the emission layer to form an electron transport layerhaving a thickness of 350 Å, LiQ was vacuum-deposited on the electrontransport layer to form an electron injection layer having a thicknessof 10 Å, and Al was vacuum-deposited on the electron injection layer toform a cathode having a thickness of 1,000 Å, thereby completing themanufacture of an organic light-emitting device.

Example 2 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that compounds shown in Table 2 were each usedinstead of Compound 1 as a dopant in forming an emission layer.

Evaluation of Example: Characterization of Organic Light-EmittingDevices

For each organic light-emitting device manufactured in Examples 1 and 2and Comparative Examples 1 to 4, a maximum value of external quantumefficiency (Max EQE), a roll-off ratio (%), and a driving voltage (V)were evaluated, and results are shown in Table 2. As evaluationapparatuses, a current-voltage meter (KEITHLEY 2400) and a luminancemeter (MINOLTA Cs-1000A) were used. The roll-off ratio was calculatedaccording to Equation 20:

Roll off ratio={1−(efficiency (at 3500 nit)/maximum emissionefficiency)}×100%  Equation 20

TABLE 2 Dopant Max EQE Roll-off ratio Driving voltage in emission layer(%) (%) (V) Example 1 Compound 1 21.5 11% 3.9 Example 2 Compound 3 22.010% 4.0 Comparative Compound A 19.0 13% 4.2 Example 1 ComparativeCompound B 20.0 16% 4.1 Example 2 Comparative Compound C 21.0 14% 4.1Example 3 Comparative Compound D 18.5 16% 4.4 Example 4

 

 

 

 

 

Referring to Table 2, it was confirmed that the organic light-emittingdevices of Examples 1 and 2 exhibited improved characteristics, such asa low driving voltage, high EQE, a decreased roll-off ratio, and a longlifespan. In addition, it was also confirmed that the organiclight-emitting devices of Examples 1 and 2 exhibited a decreasedroll-off ratio and excellent EQE and lifespan characteristics comparedto the organic light-emitting devices of Comparative Examples 1 to 4.

According to the one or more embodiments, an organometallic compound hasexcellent electrical characteristics and stability. Thus, an electronicdevice, such as an organic light-emitting device, including theorganometallic compound may have a low driving voltage, high efficiency,a long lifespan, a decreased roll-off ratio, and a FWHM of an emissionpeak of a relatively narrow EL spectrum. Therefore, the use of theorganometallic compound may enable the embodiment of a high-qualityorganic light-emitting device and an electron device including the same.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments. While one or more embodiments have beendescribed with reference to the figures, it will be understood by thoseof ordinary skill in the art that various changes in form and detailsmay be made therein without departing from the spirit and scope asdefined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein, in Formula 1, M₁ is a first-row transition metal of thePeriodic Table of Elements, a second-row transition metal of thePeriodic Table of Elements, or a third-row transition metal of thePeriodic Table of Elements, Ln₁ is a bidentate ligand, n1 is 0, 1, or 2,and Ln₂ is a ligand represented by Formula 1A, and in Formulae 1A and1-1, A₁, A₃, and A₄ are each independently a C₅-C₃₀ carbocyclic group ora C₁-C₃₀ heterocyclic group, A₂ is a 6-membered carbocyclic group or a6-membered heterocyclic group, or A₂ is a bi- or multi-cyclic C₅-C₃₀carbocyclic group including at least one of a 6-membered carbocyclicgroup and a 6-membered heterocyclic group or a bi- or multi-cyclicC₁-C₃₀ heterocyclic group including at least one of a 6-memberedcarbocyclic group and a 6-membered heterocyclic group, Y₁ is C or N, andY₂ is C or N, R₁, R₂, and R₃ are each independently a group representedby Formula 1-1, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —N(Q₄)(Q₅), —B(Q₁)(Q₂),—P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂), at least one of R₁, R₂, and R₃ is a grouprepresented by Formula 1-1, R₁₀, R₂₀, R₃₀, and R₄₀ are eachindependently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂), at least two neighboring groups among R₁₀, R₂₀, R₃₀, and R₄₀are optionally linked together to form a substituted or unsubstitutedC₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, b10 and b20 are each independently an integer from 1to 10, b30 and b40 are each independently an integer from 1 to 10, whenA₁ is a benzene group at least one of R₂₀(s) in the number of b20 is asubstituted or unsubstituted C₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃), or when A₁ is a benzene group R₁ or R₂ is a grouprepresented by Formula 1-1, * and *′ each indicate a binding site to aneighboring atom, at least one substituent of the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₇-C₆₀ arylalkyl group, the substitutedC₁-C₆₀ heteroaryl group, the substituted C₁-C₆₀ heteroaryloxy group, thesubstituted C₁-C₆₀ heteroarylthio group, the substituted C₂-C₆₀heteroarylalkyl group, the substituted C₂-C₆₀ alkylheteroaryl group, thesubstituted monovalent non-aromatic condensed polycyclic group, and thesubstituted monovalent non-aromatic condensed heteropolycyclic group is:deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, or a C₁-C₆₀ alkoxy group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group, eachsubstituted with one or more of deuterium, —F, —Cl, —Br, —I, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a C₂-C₆₀ heteroarylalkyl group, a C₂-C₆₀ alkylheteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—Ge(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group,a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,or a monovalent non-aromatic condensed heteropolycyclic group; a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, aC₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, a C₂-C₆₀alkylheteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, or a monovalent non-aromatic condensed heteropolycyclic group,each substituted with one or more of deuterium, —F, —Cl, —Br, —I, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a C₂-C₆₀ heteroarylalkyl group, aC₂-C₆₀ alkylheteroaryl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —Si(Q₂₁)(Q₂₂)(Q₂₃), —Ge(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅),—B(Q₂₆)(Q₂₇), —P(═O)(Q₁)(Q₂), or —P(Q₂)(Q₂), or —Si(Q₃₁)(Q₃₂)(Q₃₃),—Ge(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), or —B(Q₃₁)(Q₃₂), wherein Q₁ to Q₅, Q₁₁to Q₁₅, Q₂₁ to Q₂₅, and Q₃₁ to Q₃₅ are each independently hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, or a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.2. The organometallic compound of claim 1, wherein A₁ in Formula 1 is abenzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalenegroup, a benzothiophene group, a benzofuran group, an indole group, anindene group, a benzosilole group, a dibenzothiophene group, adibenzofuran group, a carbazole group, a fluorene group, or adibenzosilole group.
 3. The organometallic compound of claim 1, whereinA₂ in Formula 1 is a pyridine group, a pyrimidine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, or a phenanthroline group. 4.The organometallic compound of claim 1, wherein the organometalliccompound is a compound represented by one of Formulae 11-1 to 11-3:

wherein, in Formulae 11-1 to 11-3, M₁, n1, A₂, R₁, R₂, R₃, R₁₀, R₂₀, andb20 are each the same as described in claim 1, A₁₁ is a benzene group,an indene group, an indole group, a benzofuran group, a benzothiophenegroup, or a benzosilole group, b11 is 1, 2, 3, 4, 5, or 6, R₁₁ and R₁₂are each the same as described in connection with R₁₀ in claim 1, A₅ andA₆ are each independently a C₅-C₃₀ carbocyclic group or a C₁-C₃₀heterocyclic group, R₅₀ and R₆₀ are each independently hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₇-C₆₀ arylalkyl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂), and b50 and b60 are each independently an integer from 1 to10.
 5. The organometallic compound of claim 4, wherein in Formulae 11-1and 11-2, at least one of R₂₀(s) in the number of b20 is a substitutedor unsubstituted C₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃), or in Formulae 11-1 and 11-2, R₁ or R₂ is a grouprepresented by Formula 1-1.
 6. The organometallic compound of claim 1,wherein the organometallic compound is a compound represented by Formula12-1:

wherein, in Formula 12-1, M₁, n1, A₁, R₁, R₂, R₃, R₁₀, and b10 are eachthe same as described in claim 1, R₂₁ to R₂₄ are each independently thesame as described in connection with R₂₀ in claim 1, A₅ and A₆ are eachindependently a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group,R₅₀ and R₆₀ are each independently hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted C₂-C₆₀heteroarylalkyl group, a substituted or unsubstituted C₂-C₆₀alkylheteroaryl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —Ge(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), or—P(Q₂)(Q₂), and b50 and b60 are each independently an integer from 1 to10.
 7. The organometallic compound of claim 6, wherein in Formula 12-1,when A₁ is a benzene group, at least one of R₂₁ to R₂₄ is a substitutedor unsubstituted C₁-C₆₀ alkyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃), or in Formula 12-1, when A₁ is a benzene group, R₁ orR₂ is a group represented by Formula 1-1.
 8. The organometallic compoundof claim 1, wherein R₁, R₂, and R₃ are each independently a grouprepresented by Formula 1-1, hydrogen, deuterium, a methyl group, anethyl group, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, atert-pentyl group, a neo-pentyl group, a 3-pentyl group, a3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C₁-C₂₀alkylphenyl group, a naphthyl group, —Si(Q₁)(Q₂)(Q₃), or—Ge(Q₁)(Q₂)(Q₃), and at least one of R₁, R₂, and R₃ is a grouprepresented by Formula 1-1.
 9. The organometallic compound of claim 1,wherein R₂ is a group represented by Formula 1-1, and each of R₁ and R₃is hydrogen.
 10. The organometallic compound of claim 1, wherein R₁₀,R₂₀, R₃₀, and R₄₀ are each independently a group represented by one ofFormulae 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to10-350:

wherein, in Formulae 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and10-201 to 10-350, * indicates a binding site to a neighboring atom, Phis a phenyl group, TMS is a trimethylsilyl group, and TMG is atrimethylgermyl group.
 11. The organometallic compound of claim 1,wherein the organometallic compound is represented by at least one ofFormulae 21-1 to 21-5:

wherein, in Formulae 21-1 to 21-5, M₁, n1, and R₁ to R₃ are each thesame as described in connection with claim 1, X₁ is O, S, N(R₁₅),C(R₁₅)(R₁₆), or Si(R₁₅)(R₁₆), R₁₁ to R₁₆ are each independently the sameas described in connection with R₁₀ in claim 1, R₂₁ to R₂₄ are eachindependently the same as described in connection with R₂₀ in claim 1,and R₅₁ to R₅₄ and R₆₁ to R₆₄ are each independently the same asdescribed in connection with R₁₀ in claim
 1. 12. The organometalliccompound of claim 1, wherein ligand Ln₂ in Formula 1 is represented byone of Formulae 2-1 to 2-27:

wherein, in Formulae 2-1 to 2-27, X₁ is O, S, N(R₁₅), C(R₁₅)(R₁₆), orSi(R₁₅)(R₁₆), R₁₅ and R₁₆ are each independently the same as describedin connection with R₁₀ in claim 1, R₂₂ and R₂₃ are each independently aC₁-C₂₀ alkyl group, —Si(Q₅₁)(Q₅₂)(Q₅₃), or —Ge(Q₅₁)(Q₅₂)(Q₅₃), Q₅₁ to Qare each independently a C₁-C₂₀ alkyl group, R₃₁ to R₃₄ are eachindependently the same as described in connection with R₃₀ in claim 1,R₄₁ to R₄₄ are each independently the same as described in connectionwith R₄₀ in claim 1, and * to *′ each indicate a binding site to M₁. 13.The organometallic compound of claim 1, wherein the organometalliccompound does not comprise an amine group.
 14. The organometalliccompound of claim 1, wherein the organometallic compound is a compoundrepresented by one of Compounds 1 to 36:


15. An organic light-emitting device comprising: a first electrode; asecond electrode, and an organic layer arranged between the firstelectrode and the second electrode and comprising an emission layer,wherein wherein the organic layer comprises at least one organometalliccompound of claim
 1. 16. The organic light-emitting device of claim 15,wherein the emission layer comprises the at least one organometalliccompound.
 17. The organic light-emitting device of claim 16, wherein theemission layer further comprises a host, and an amount of the host isgreater than an amount of the at least one organometallic compound inthe emission layer.
 18. The organic light-emitting device of claim 17,wherein the emission layer emits green light having a maximum emissionwavelength of about 500 nanometers to about 600 nanometers.
 19. Theorganic light-emitting device of claim 15, wherein the first electrodeis an anode, the second electrode is a cathode, the organic layerfurther comprises a hole transport region between the first electrodeand the emission layer and an electron transport region between theemission layer and the second electrode, the hole transport regioncomprises a hole injection layer, a hole transport layer, an electronblocking layer, a buffer layer, or a combination thereof, and theelectron transport region comprises a hole blocking layer, an electrontransport layer, an electron injection layer, or a combination thereof.20. An electronic apparatus comprising the organic light-emitting deviceof claim 15.